Sodium Carbonate → HCID 178424919, compound

HRID 251648Notes

Reaction equation

HRID 251648 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:4]([O:21][CH:22]([CH3:24])[CH3:23])[CH:3]=1.[CH:25]([C:28]1[C:36]2[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][C:31]=2[NH:30][N:29]=1)([CH3:27])[CH3:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]([O:21][C:4]1[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:6]([CH3:8])[N:7]=[C:2]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:36]=2[C:28]([CH:25]([CH3:27])[CH3:26])=[N:29][NH:30]3)[CH:3]=1)([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 865939916-Chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridineHCID 178440403HCID 178440403, compound

Product 1

HCID 178424919HCID 178424919, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridine (185 mg, 0.53 mmol), 3-isopropyl-1H-indazole-4-boronic acid (109 mg, 0.53 mmol), Pd(PPh3)4 (31 mg, 0.027 mmol), and Na2CO3 (169 mg, 1.6 mmol) in dioxane (8 mL) and water (2 mL) is heated for 24 hours at 100° C. The mixture is poured into water and extracted with EtOAc. The combined extract are dried (Na2SO4) and concentrated in vacuo. The residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10) to yield 4-[4-isopropoxy-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyridin-2-yl]-3-isopropyl-1H-indazole. 1H NMR (CDCl3) 9.95 (br s, 1H), 7.45 (d, 1H), 7.39 (t, 1H), 7.13 (d, 1H), 7.09 (d, 1H), 6.92 (m, 2H), 6.78 (d, 1H), 5.20 (s, 2H), 4.68 (m, 1H), 3.19 (m, 1H), 2.88 (m, 1H), 2.64 (s, 3H), 2.20 (s, 3H), 1.99 (d, 6H), 1.24 (d, 6H), 1.11 (d, 6H). LCMS (m/z): 472.63 (MH)+

Workup

  1. extractionextracted with EtOAc
  2. extractionThe combined extract
  3. dry with materialare dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10)

Sources & evidence

ORD record
ord-7d378f50dae94e65bca17964d149e7aa
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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